Unfiltered Leadership with Lindsay Yellin

26. People Pleasing Almost Broke Me — Here's What I Had to Unlearn

I spent years making everyone comfortable, and for a long time, it worked. It made me good at reading rooms, smoothing tension, staying dependable, and being the person people could count on. But as I sat down for this solo birthday episode, reflecting on one of the hardest years of my life, I realized how much of that “strength” was actually my people pleaser trying to keep me safe. What I’m learning is that people pleasing can look like leadership, kindness, and strength from the outside, while underneath it can become self-abandonment. When your need to be liked starts overriding your values, your presence, your boundaries, and your ability to ask for help, something has to change. If you are a high-achieving people pleaser who is exhausted from fixing, managing, performing, and keeping everyone else comfortable, I hope this feels like a hand on your shoulder. We’re talking about how to stop people-pleasing, how to sit with the discomfort of disappointing others, and how to reclaim your needs before burnout makes the choice for you. Inside this episode • Why this birthday reflection brought my people-pleasing into focus • Why people-pleasing can become a career survival strategy • The leadership cost of staying silent to keep the peace • How managing everyone’s emotions keeps you from being present • Why is no one pleased when you stop pleasing • How to reclaim your values, boundaries, and needs without losing your worth

25. Leading Like a Coach: Listening, Vulnerability, and Letting Go of Control with Caitlin Golden

In this episode of Unfiltered Leadership, Lindsay sits down with Caitlin Golden, HR executive and longtime friend, for a deep conversation about coaching, leadership, vulnerability, and what it really means to lead people well. Lindsay and Caitlin first met through the Co-Active Training Institute during coach training while both were still working in advertising and marketing. What started as professional curiosity evolved into a years-long friendship grounded in shared values around people-centered leadership and personal growth. Together, they explore how coaching fundamentally changed the way they lead, listen, communicate, and show up in relationships at work. This conversation dives into: * why most people hear but don’t truly listen * how curiosity creates stronger leadership * the difference between fixing and supporting * vulnerability, accountability, and trust in leadership * why great managers see people as whole humans * and how self-awareness changes the way we lead others Caitlin also shares practical examples from her experience leading HR teams, conducting exit interviews, managing talent, and helping people grow through feedback and recognition. This episode is a powerful reminder that leadership isn’t about having all the answers. It’s about being willing to listen deeply, stay curious, and create spaces where people feel seen, heard, and understood. About your host: Lindsay Yellin Lindsay Yellin is an executive leadership coach, dynamic speaker, and certified ACC and CPCC who helps high-achieving creative leaders trade fear for possibility and self-doubt for self-trust. A former advertising executive, she has led in high-pressure, high-visibility environments and knows the challenge of staying connected to oneself while leading others. ✨ Book a Coaching Chemistry Call with Lindsay: https://calendly.com/yellin-coaching/chemistry-call [https://calendly.com/yellin-coaching/chemistry-call]  ✨ Get your espresso shot of leadership insight, join the Grounds for Growth newsletter: https://yellingroundsforgrowth.myflodesk.com/groundsforgrowth [https://yellingroundsforgrowth.myflodesk.com/groundsforgrowth]  About Caitlin Golden Caitlin is a senior HR executive with nearly two decades of experience building people-first cultures inside fast-moving agencies and startups. A Co-Active trained coach, she brings that same whole-person philosophy into her leadership work — helping organizations and the individuals within them grow from the inside out. Her practice sits at the intersection of strategic HR and human development, with a particular focus on leadership, engagement, and building the kind of environments where people genuinely thrive. Episode Highlights * How Lindsay and Caitlin met through coach training * Why coach training was “life changing” for both of them * The difference between hearing and truly listening * What “powerful questions” actually look like * Why curiosity is one of the most underrated leadership skills * How coaching changes the way you manage teams * The danger of leaders trying to fix everything * Why strong leaders guide instead of control * The connection between self-awareness and emotional intelligence * How to “read the room” by understanding yourself first * Why great leaders admit when they don’t know something * The role of vulnerability, accountability, and repair in leadership * How acknowledgment and recognition transform team culture * Why people-centered leadership creates stronger engagement and trust * Letting go of ego, perfectionism, and control as a leade

24. 5 Leadership Behaviors That Changed My Career

In this solo episode of Unfiltered Leadership, Lindsay reflects on five leaders who fundamentally changed the trajectory of her life and career by believing in her before she fully believed in herself. From her early days in advertising to her transition into coaching and leadership development, Lindsay shares the moments, conversations, and leadership behaviors that shaped how she leads today. This episode is both deeply personal and highly practical, unpacking what great leadership actually looks like in action: * Sponsorship over surface-level mentorship * Creating psychological safety * Championing the whole person * Speaking possibility into others * Helping people step into rooms before they feel fully ready Through stories about 5 leaders who impacted her career, Lindsay explores how belief can change someone’s trajectory and how leaders have the opportunity to create those moments every single day. If you’ve ever wondered what truly impactful leadership looks like, this episode is a reminder that sometimes the smallest moments of belief become the biggest turning points. * Why the best leaders don’t just mentor, they sponsor * The difference between giving advice and creating access * How Jessica Henrichs helped Lindsay see her own leadership potential * Why speaking your ambitions out loud can change your life * Ronnie Dickerson Stewart’s role in Lindsay becoming a coach * The power of sharing your goals with the right people * How Amy Cheronis helped Lindsay launch her coaching career * Why leaders should create environments where people feel safe asking before they’re ready * Chris Loeffler’s approach to people-first leadership * Why some performance problems are actually role-fit problems * Joan Vivaldelli’s role in Lindsay becoming a leadership facilitator * Why confidence comes after action, not before * The importance of believing in others before they fully believe in themselves About your host: Lindsay Yellin Lindsay Yellin is an executive leadership coach, dynamic speaker, and certified ACC and CPCC who helps high-achieving creative leaders trade fear for possibility and self-doubt for self-trust. A former advertising executive, she has led in high-pressure, high-visibility environments and knows the challenge of staying connected to oneself while leading others. ✨ Book a Coaching Chemistry Call with Lindsay: https://calendly.com/yellin-coaching/chemistry-call [https://calendly.com/yellin-coaching/chemistry-call]  * ✨ Get your espresso shot of leadership insight, join the Grounds for Growth newsletter: https://yellingroundsforgrowth.myflodesk.com/groundsforgrowth [https://yellingroundsforgrowth.myflodesk.com/groundsforgrowth]

23. Tenacity, Storytelling, and Leadership: Real Talk on Careers and Growth with Amy Cheronis

In this episode of Unfiltered Leadership, Lindsay sits down with Amy Cheronis, advertising and PR leader and co-founder of The Scratch Collective, for a wide-ranging conversation on leadership, mentorship, and building a meaningful career over time. Amy was also Lindsay’s very first executive coaching client, making this conversation a full-circle moment grounded in trust, growth, and shared history. Together, they explore what it means to lead in today’s advertising and communications industry, not just through performance, but through how you show up for others. Amy shares how she actively creates access for emerging talent, what makes someone stand out early in their career, and why tenacity, clarity, and thoughtful communication matter more than ever. They also go beyond early careers, diving into: * how to build a career that evolves with you * the importance of storytelling in shaping your path * why leadership is about investing in others * and how to navigate uncertainty, change, and growth over time This episode is both practical and deeply human, offering insights for anyone at any stage of their career, whether you’re just starting out, leading teams, or rethinking what’s next. About your host: Lindsay Yellin Lindsay Yellin is an executive leadership coach, dynamic speaker, and certified ACC and CPCC who helps high-achieving creative leaders trade fear for possibility and self-doubt for self-trust. A former advertising executive, she has led in high-pressure, high-visibility environments and knows the challenge of staying connected to oneself while leading others. ✨ Book a Coaching Chemistry Call with Lindsay: https://calendly.com/yellin-coaching/chemistry-call [https://calendly.com/yellin-coaching/chemistry-call]  ✨ Get your espresso shot of leadership insight, join the Grounds for Growth newsletter: https://yellingroundsforgrowth.myflodesk.com/groundsforgrowth [https://yellingroundsforgrowth.myflodesk.com/groundsforgrowth]  About Amy Cheronis Amy is a global communications and stakeholder engagement pro who co-founded The Scratch Collective after working and leading at top agencies Leo Burnett, DDB and MSL. For the past five years, she has delivered business-building PR, executive visibility, social media, influencer marketing and corporate communications for both iconic and niche brands at Scratch. Her sweet spot is personal brand work for the C-suite, coaching and advising leaders from Kimberly-Clark, Nature’s Fynd, Shiru, Ulta Beauty and Wow Bao. Amy lives in Chicago with her husband, three teenagers and in close proximity to other favorite things - Lake Michigan, tennis and golf. Connect with Amy on LinkedIn https://www.linkedin.com/in/amycheronis/ [https://www.linkedin.com/in/amycheronis/] Learn more about The Scratch Collective www.thescratchcollective.com [http://www.thescratchcollective.com] Episode Highlights * Lindsay and Amy’s full-circle journey from coaching client to podcast guest * What leadership looks like in practice through mentorship and access * How Amy supports emerging advertising and PR professionals * What actually makes someone stand out early in their career * The importance of tenacity, consistency, and polish * Why networking is about clarity and intentionality * How to make thoughtful, direct asks that build real relationships * The role of storytelling in shaping your career path * Why you don’t have to start exactly where you want to * How every role builds skills, perspective, and future opportunity * Navigating change, growth, and evolving identity in your career

22. Using Fun to Identify Your Purpose with Matt Allyn

In this episode of Unfiltered Leadership, Lindsay sits down with Matt Allyn to explore the patterns, beliefs, and internal narratives that keep us stuck and why fun, curiosity, and play might be the missing ingredients in creating real change. Matt brings a unique perspective shaped by his unconventional path. From biking across the United States to working as a Crossfit photographer, his career has been rooted in exploration, discipline, and pushing physical and mental limits. Those experiences deeply inform how he thinks about growth, resilience, and behavior change. Together, Lindsay and Matt unpack why awareness alone isn’t enough to create transformation, how we get trapped in rigid patterns, and how introducing lightness and experimentation can help us shift more effectively. This conversation is both practical and refreshing, offering a new way to think about personal growth that feels less heavy and more human. Episode Highlights * Why we stay stuck in patterns even when we know better * The gap between awareness and lasting behavior change * How Matt’s experience biking across the U.S. shaped his mindset * Why fun, curiosity, and play are critical for growth * How internal narratives influence leadership and decision-making * Practical ways to interrupt patterns and experiment with change About your host: Lindsay Yellin Lindsay Yellin is an executive leadership coach, dynamic speaker, and certified ACC and CPCC who helps high-achieving creative leaders trade fear for possibility and self-doubt for self-trust. A former advertising executive, she has led in high-pressure, high-visibility environments and knows the challenge of staying connected to oneself while leading others. ✨ Book a Coaching Chemistry Call with Lindsay: https://calendly.com/yellin-coaching/chemistry-call [https://calendly.com/yellin-coaching/chemistry-call]  ✨ Get your espresso shot of leadership insight, join the Grounds for Growth newsletter: https://yellingroundsforgrowth.myflodesk.com/groundsforgrowth [https://yellingroundsforgrowth.myflodesk.com/groundsforgrowth]  About Matt Allyn Matt Allyn is the founder of Storyliving which helps leaders use their story to prioritize fun so they can change the world. In 2016 he was a civil engineer in NYC when he decided to ride his bike across America. This decision changed his life. He knew his greatest contribution to the world would come from prioritizing fun and joy, and only then would he be able to truly impact in the world for the better. You can view Matt’s Storylivng workshop here: https://matthewallyn.me/slt [https://matthewallyn.me/slt]